Does anyone have any tips and tricks to share for repairing gel-coat chips and dings in the daggerboard wells, or is it all just a lot of patience? I've been trying to go after a few on my boat, and its a royal pain...

Your gonna need to get sandpaper down in there with a stick or better yet a dremel with a long reach to grind out the area and bevel. Use a custom tool to get the glass or mixed resin (with glass beads or something) onto the area and hold it. A bit of mold release on the tool will help. Maybe the tool is shaped like your pocket "V". of course the more you make a mess, the more you have to grind out later Patience is your friend.